Not sure if you’re visiting or local, but if you’re going to spend some time here I cannot recommend the Connecticut Forest and Park Association’s hike book enough:
Connecticut Walk Book: The Complete Guide to Connecticut's Blue-Blazed Hiking Trails https://www.amazon.com/dp/0819577146/ref=cm_sw_r_awdo_Q9B4PQE3SCT5B1CVY9AS?psc=1
The older version was better, it was a binder where you could remove pages, but this book will give you the best of Connecticut hikes to sink your teeth into.
I will also tell you that if you are up for a drive, hiking out and spending the night in the Riga shelter on the Appalachian trail in western Connecticut is pretty great:
http://thenortheasthiker.com/2018/11/01/riga-shelter-on-the-appalachian-trail-in-connecticut/